DETAILED ACTION
Status of Application
This action is responsive to nonprovisional application filed 12/07/2023. Original claims 1-20 are currently pending and under examination herein.
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA . However, in the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for a rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
Information Disclosure Statement(s)
The information disclosure statement(s) (IDS) filed on 12/07/2023 and 10/01/2025 are in compliance with the provisions of 37 CFR 1.97, 1.98 and MPEP § 609, and therefore the information referred to therein has been considered as to the merits. Initialed copies of the IDS are included with the mailing/transmittal of this Office action.
Claim Rejections – 35 U.S.C. 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 16-18 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Regarding Claim 16, the limiting significance of the expression “used in a fuel cell, … or a CO2 separator” is unclear. The claim is ostensibly directed to an anion exchange membrane and it is not apparent whether the alternative “used in” recitations are intended to imply additional structural limitation(s) beyond the positively recited membrane elements, or are merely non-limiting statements of intended uses thereof. In the latter case, the various intended use statements fail to create a substantive difference in scope vis-à-vis parent claim 15/1, as required by 37 CFR 1.75(b), while engendering ambiguity as to which category of invention (anionic exchange membrane as article or method of using same) the claim is actually directed to. Clarification and appropriate correction are required.
Regarding Claims 17/18, the term “thin” in each claim is a relative term which renders the claims indefinite. That is, the term is not defined by either claim, the specification is not found to provide a definition or standard for ascertaining the requisite film thicknesses, and, thus, one of ordinary skill in the art would not be reasonably apprised of the scope of the invention.
Common Ownership Notice
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim Rejections – 35 U.S.C. 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1-2, 5-6, 8-9, 12 and 15 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Olsson, et al (Journal of Membrane Science, 578 (2019) 183-195) (hereinafter, ‘Olsson’).
Regarding Claims 1-2, 5-6, and 15, reference to Olsson has already disclosed anion exchange membranes [for claim 15] based on partly quaternized poly(biphenyl N-methylpiperidine) (PBPip), see section 3.2. Partial quaternizations; Scheme 1, Series 1 (p. 187), Table 1 (p. 188) and section 4. Conclusions. Series 1 non-crosslinked PBPipQs are characterized by a plurality of repeating units of structural formula:
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(see Scheme 1) where x indicates the molar percentage of quaternary (dimethylated) piperidinium rings (see p. 186, first para of right-hand column). Olsson in Table 1 reports certain properties of five specific Series 1 polymers, including PBPipQ35%, which corresponds identically to claimed formula (I) when: Ar1 and Ar2 are each
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; X1 is
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, X2 is
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, Ar1 and Ar2 are the same, Y1- is OH- anion [for claim 5], R1-R12 are each hydrogen, R30 and R31 are each -CH3 [for claims 5, 6], the molar ratio of n/m is in a range of 1:1 to 99:1 (viz., 1.86), and q is 0.
Regarding Claims 8-9 and 12, Olsson further discloses that the PBPipQx% polymers, including aforementioned PBPipQ35%, are synthesized from biphenyl and N-methyl-4-piperidone (see Scheme 1, Series 1). The former is identical to claimed monomers Ar1’ and Ar2’ where q is 0, Ar1’ and Ar2’ are the same, and R1-R12 are each hydrogen [for claims 8/9]; while the latter is identical to claimed monomer X1’ when selected from
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where R30 is an alkyl group (viz., -CH3) [for claim 12].
Claim Rejections – 35 U.S.C. 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
Claims 4, 7, 13-14, and 16-20 are rejected under 35 U.S.C. 103 as being unpatentable over Olsson in view of Yan et al (US 2019/0036143 A1) (hereinafter, ‘Yan’).
Regarding Claim 4, Olsson discloses the anion exchange polymer of claim 1 as discussed above. Olsson does not directly disclose wherein Ar1 and Ar2 are selected from the group consisting of:
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Olsson instead describes partly quaternized poly(biphenyl N-methylpiperidine) (PBPip) polymers, such as the aforementioned PBPipQ35%.
However, in the same technical field involving poly(aryl piperidinium) polymers for use in hydroxide exchange membrane fuel cells (see Abs., ¶ [0003]), Yan teaches that the poly(aryl piperidinium) polymer comprises a reaction product of a polymerization mixture comprising (i) either a piperidone monomer or a 3-oxo-6-azoniaspiro[5.5]undecane salt monomer, (ii) an aromatic monomer, and (iii) optionally, a trifluoroacetophenone monomer (see ¶ [0048]). As specific examples of the aromatic monomer, Yan illustrates synthesis of poly(aryl piperidinium) polymers comprising a reaction product of a polymerization mixture comprising: N-methyl piperidone, 2,2,2-trifluoroacetophenone and biphenyl (Example 1) or terphenyl (Example 2) (Yan, ¶¶ [0088]-[0102]). As such, Yan effectively teaches the claimed terphenyl structure (
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) as a viable equivalent to the biphenyl monomer of Olsson. Accordingly, it would have been obvious to one of ordinary skill in the art at the time of effective filing to have modified Olsson by substituting the biphenyl monomer by terphenyl as per Yan, prompted by the predictable outcome of obtaining an anion exchange polymer displaying equivalent utility in fuel cell applications. Simple substitution of one known element for another to obtain predictable results, provides the rationale for a prima facie case of obviousness. See MPEP § 2143. Further, the proposed substitution will meet all the requirements of claim 4.
Regarding Claims 7 and 13, Olsson discloses the anion exchange membrane of claim 8 as discussed above. Olsson does not directly disclose wherein X2 is a mixture of
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wherein R₃₀ is -H, -CH₃, -CH2CH₃, -CH(CH₃)₂, -C(CH₃)₃, -CH₂-C₆H₅, or -CH₂-CH(CH₃)₂; and wherein R₃₂ is -C₆H₅; and wherein t is 1, 2, 3, 4, 5, or 6 [per claim 7]; or wherein X1’ is a mixture of
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wherein R₃₀ is -H, -CH₃, -CH2CH₃, -CH(CH₃)₂, -C(CH₃)₃, -CH₂-C₆H₅, or -CH₂-CH(CH₃)₂; and wherein R₃₂ is -C₆H₅; and wherein t is 1, 2, 3, 4, 5, or 6 [per claim 13].
Olsson does, however, describe synthesis of completely quaternized copolymers by co-polyhydroxyalkylations of N-methyl-4-piperidone and biphenyl with pre-determined stoichiometric ratios of either 1,1,1-trifluoroacetone (TFAc) or 1,1,1-fluoroacetophenone (TFAp) (see section 3.3 Copolymerizations). TFAp corresponds to claimed mixture component
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and the corresponding quaternized copolymer (Series 2) comprises TFAp residues corresponding to claimed mixture component
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. With respect to the Series 2 samples, Olsson notes that the introduction of hydrophobic units containing TFAc and TFAp residues led to a lower water uptake at similar IECs, compared with the partly quaternized PBPipQ samples of Series 1 (see p. 191, final full para). Yan similarly shows that the water content of three poly(aryl piperidinium) (PDP) samples is inversely related to the mole ratio of N-methyl-4-piperidone to 2,2,2-trifluoroacetophenone in the polymerization mixture, such that the PDP sample with the highest content of TFAp (PAP-1-50) exhibited the lowest water uptake (see Yan, FIG. 6 and ¶ [0094]). Thus, one of ordinary skill in the art seeking to reduce water uptake of the partly quaternized PBPipQs of Olsson would have found it obvious to modify the disclosed Series 1 synthesis by polymerizing biphenyl with a mixture with N-methyl-4-piperidone (NMP) and TFAp in proportions optimized in consideration of the desired reduction in water uptake of the resulting polymer. And since such mixture of NMP and TFAp corresponds to the claimed X1’ mixture, and since the resultant polymer would comprise NMP and TFAp residues corresponding to the claimed X2 mixture, the proposed modification would satisfy all requirements of claims 7 and 13.
Regarding Claim 14, Olsson discloses the anion exchange membrane of claim 8 as discussed above. Olsson does not directly disclose X1’ is a mixture of
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wherein R₃₀ is -H, -CH₃, -CH₂CH₃, -CH(CH₃)₃, -CH₂-C₆H₅, or -CH₂-CH(CH₃)₂; and wherein t is 1, 2, 3, 4, 5, or 6;
wherein Y₂⁻ is HCO3-, OH-, I-, CF3SO3-, or
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; and
wherein R50 is -CH₃, -CF₃, CH3CH2-, or CH3CH2CH2-.
However, as discussed above with respect to claim 4, Yan teaches to provide a poly(aryl
piperidinium) polymer comprising a reaction product of a polymerization mixture comprising (i) either a
piperidone monomer or a 3-oxo-6-azoniaspiro[5.5]undecane salt monomer, (ii) an aromatic monomer,
and (iii) optionally, a trifluoroacetophenone monomer (see ¶ [0048]). The piperidone monomer and the
3-oxo-6-azoniaspiro[5.5]undecane salt monomer correspond to respective mixture components of X1' in claim 14, (see ¶ [0055]). Yan thus teaches the two monomer types as individually suitable in forming poly(aryl piperidinium) polymers capable of forming anion-exchange membranes. Olsson similarly aims to provide anion-exchange membranes obtained from partially quaternized poly(biphenyl N-methylpiperidine) (PBPip) synthesized by polyhydroxyalkylation of N-methyl-4-piperidone and biphenyl (see sections 3.1-3.2 and pp. 187-188, bridging para). It would have been obvious to one of ordinary skill in the art at the time of effective filing to have modified Olsson by substituting the N-methyl-4-piperidone monomer with a mixture of a piperidone monomer and a 3-oxo-6-azoniaspiro[5.5]undecane salt monomer as per Yan, prompted by the predictable outcome of obtaining an equivalent anion exchange polymer. Indeed, it has been held that combining art-recognized equivalents known for the same purpose is prima facie obvious. See MPEP § 2144.06(I).
Regarding Claims 16-18, Olsson discloses the anion exchange membrane of claim 1 as discussed above. Olsson does not directly disclose wherein the anion exchange membrane comprises a nonporous symmetric dense film membrane, an integrally-skinned asymmetric membrane, a reinforced composite membrane, or a thin film composite membrane, as recited claim 17. However, Olsson characterizes the synthetic strategies described therein as important for the preparation of functional high-performance AEMs for different electrochemical applications, including fuel cell evaluations (see section 4. Conclusions); further, it is known from Yan that anion exchange membranes comprising poly(aryl piperidinium) polymers are suitable for use in fuel cells (Yan, ¶¶ [0029], [0081]-[0082], [0085]). In that context, Yan teaches that the poly(aryl piperidinium) polymers can be made into reinforced hydroxide exchange membranes [for claim 18] comprising a porous substrate impregnated or coated with the anion exchange polymer (Yan, ¶¶ [0069], [0077], [0081], [0109] (Ex. 9)) [for claim 19]. Inasmuch as Olsson similarly aims to provide functional, high-performance AEMs for electrochemical applications, including fuel cell evaluations, as noted above, it would have been obvious to one of ordinary skill in the art at the time of effective filing to have utilized any of the PBPipQx% membranes of Olsson, in the form of a reinforced composite membrane as per Yan, as the AEM of a fuel cell (i.e., “in a fuel cell,” per claim 16), with a reasonable expectation of success.
Regarding Claims 19-20, Olsson discloses the anion exchange polymer of claim 1 as discussed above. Olsson further discloses anion exchange membranes (AEMs) obtained from such anion exchange polymer, in particular PBPipQ35%, PBPipQ42%, PBPipQ52%, PBPipQ62% and PBPipQ77% (see pp. 187-188, bridging para and Table 1, Series 1). Olsson further recognizes the current development of AEMs for use in alkaline anion exchange membrane fuel cells (AEMFCs), among other uses (see section 1. Introduction), but does not directly disclose a membrane electrode assembly as defined in claims 19 and 20. Nevertheless, the conventionality of utilizing poly(aryl piperidinium) polymers as the anion exchange membrane of a fuel cell assembly as claimed is well known in the art as taught by Yan. Thus, Yan discloses a membrane electrode assembly (fuel cell 10 in FIG. 1 and Yan ¶ [0082]) comprising: an anion exchange membrane (membrane electrolyte 16 in FIG. 1 and Yan ¶ [0082]) comprising an anion exchange polymer; an anode (anode portion 12 in FIG. 1 of Yan) comprising an anode catalyst (element 26 in FIG. 1 of Yan) on a first surface of the anion exchange membrane (see FIG. 1, reproduced below); a cathode (cathode portion 14 in FIG. 1 of Yan) comprising a cathode catalyst (element 28 in FIG. 1 of Yan) on a second surface of the anion exchange membrane (membrane electrolyte 16 in FIG. 1 of Yan); a gas diffusion layer adjacent to the cathode (element 20 in FIG. 1 of Yan; taken as equivalent to “cathode porous transport layer” of claim 20); and a gas diffusion layer adjacent to the anode (element 18 in FIG. 1 of Yan; taken as equivalent to “anode porous transport layer” of claim 20).
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Given Olsson’s recognition that AEMs are currently being developed for use in AEMFCs, as noted above, and his characterization of the synthetic strategies described therein as important for the preparation of functional high-performance AEMs for different electrochemical applications, including fuel cell evaluations (see section 4. Conclusions), an ordinarily skilled practitioner would have
had a reasonable expectation of the disclosed PBPipQx% membranes being viable candidates for the membrane electrolyte of a membrane electrode assembly such as disclosed by Yan. Accordingly, it would have been obvious to one of ordinary skill in the art at the time of effective filing to have utilized the anion exchange polymer of present claim 1, as disclosed by Olsson, as the anion exchange membrane of a membrane electrode assembly as per Yan, with a reasonable expectation of success.
Allowable Subject Matter
Claims 3 and 10-11 are objected to as being dependent on a rejected base claim, but would be allowable if rewritten in independent form including all the limitations of the base claim and any intervening claim.
The following is a statement of reasons for the indication of allowable subject matter:
The closest prior art to Olsson et al and Yan et al, discussed above, does not describe the inventions of claims 3, 10, and 11, especially the particular fused ring species recited for Ar1 and Ar2 (claim 3) and for Ar1’ and Ar2’ (claims 10-11), or provide proper rationale for modifying either of their respective inventions to arrive at the invention of claim 3, 10 or 11.
Further as to CN11130360A (CN ‘360) (cited in ISR from corresponding PCT application), the document discloses an anion exchange polymer comprising a phenanthrene structural unit represented by formula (1A) and/or formula (2A), and a piperidine quaternary ammonium structural unit represented by formula (3A) (¶¶ [0036]-[0039]). In a preferred embodiment, the anion exchange polymer further includes an aryl structural unit represent by formula (4A) and/or formula (5A) (¶¶ [0043]-[0045]). CN ‘360 does not teach an anion exchange polymer comprising a plurality of repeating units of instant formula (I), especially in regards to variable X2 as defined in present claim 1. Furthermore, while said formula (4A) encompasses a biphenyl structural unit such as used in Olsson et al, CN ‘360 does not teach or suggest an equivalency between the phenanthrene structural unit and the biphenyl structural unit such that the former may be substituted by the latter in the main chain of the anion exchange polymer. Instead, CN ‘360 teaches that the phenanthrene structural unit is an essential constituent in all embodiments of its anion exchange polymer, and that the aryl structural unit may be absent in certain embodiments thereof. As such, CN ‘360 does not provide proper rationale for modifying its invention or the disclosures of Olsson et al or Yan et al so as to arrive at the invention of present claim 3, 10 or 11.
Correspondence
Any inquiry concerning this communication should be directed to Examiner F. M. Teskin whose telephone number is (571) 272-1116. The examiner can normally be reached on Monday through Friday from 9:00 AM - 5:30 PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Robert Jones, can be reached at (571) 270-7733. The appropriate fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/FRED M TESKIN/Primary Examiner, Art Unit 1762
/FMTeskin/07-22-26
Prosecution Insights